Tetrahydrofuran → HCID 57956847, compound

HRID 2172816Notes

Reaction equation

HRID 2172816 reaction equation
[OH:1][C:2]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11](=O)[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[CH:9][CH:10]=1.[CH2:29]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:1][C:2]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11](=[CH2:29])[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 57956828HCID 57956828, compound

Product 1

HCID 57956847HCID 57956847, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a suspension of methyltriphenylphosphonium bromide in THF is added KOBu-t (1 M in THF, 6.1 mmol) at room temperature. After stirring for 30 mins, tert-butyl 3-(3-(3-hydroxy-3-propylhexyl)phenyl)-3-oxopropylcarbamate is added. The resulting mixture is stirred at room temperature for 18 h. The reaction is quenched by the addition of AcOH. The mixture is filtered and concentrated under reduced pressure. Purification by flash chromatography (15 to 50% EtOAc-hexanes gradient) gives tert-butyl 3-(3-(3-hydroxy-3-propylhexyl)phenyl)but-3-enylcarbamate.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 18 h
  2. customThe reaction is quenched by the addition of AcOH
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (15 to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-f65b91c31a9e4d6380da76c6bf501ddb
Source dataset
uspto-grants-2015_06
Patent number
US09056849B2

Reaction notes

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